Details
Stereochemistry | ACHIRAL |
Molecular Formula | C20H25N3S |
Molecular Weight | 339.498 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCN(CCCN2C3=C(SC4=C2C=CC=C4)C=CC=C3)CC1
InChI
InChIKey=WEYVCQFUGFRXOM-UHFFFAOYSA-N
InChI=1S/C20H25N3S/c1-21-13-15-22(16-14-21)11-6-12-23-17-7-2-4-9-19(17)24-20-10-5-3-8-18(20)23/h2-5,7-10H,6,11-16H2,1H3
Molecular Formula | C20H25N3S |
Molecular Weight | 339.498 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.ncbi.nlm.nih.gov/pubmed/16625562Curator's Comment: Description was created based on several sources, including
http://www.ncbi.nlm.nih.gov/pubmed/12523495 and http://www.genome.jp/dbget-bin/www_bget?D01412
Sources: http://www.ncbi.nlm.nih.gov/pubmed/16625562
Curator's Comment: Description was created based on several sources, including
http://www.ncbi.nlm.nih.gov/pubmed/12523495 and http://www.genome.jp/dbget-bin/www_bget?D01412
Perazine (Taxilan) is a moderate-potency typical antipsychotic of the phenothiazine class. Perazine is an older antipsychotic drug first introduced in the 1950s. It is suggested to have a low level of side effects (especially for movement disorders). Its use is regional and restricted to countries like Germany, Poland, the Netherlands and the former Yugoslavia. Perazine has being shown to be a potent inhibitor of human CYP1A2. It acts as a dopamine antagonist.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL3356 Sources: http://www.ncbi.nlm.nih.gov/pubmed/12523495 |
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Target ID: CHEMBL217 Sources: http://www.genome.jp/dbget-bin/www_bget?D01412 |
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Target ID: Cytochrome P450 2B, Rattus norvegicus Sources: http://www.ncbi.nlm.nih.gov/pubmed/18048963 |
45.0 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Taxilan Approved UseTaxilan is used in the treatment of schizophrenia |
PubMed
Title | Date | PubMed |
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[Electroconvulsive therapy in treatment of acute life threatening catatonia in toxic epidermal necrolysis (Lyell syndrome)]. | 1992 May |
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Cytochrome P-450 enzymes and FMO3 contribute to the disposition of the antipsychotic drug perazine in vitro. | 2000 Sep |
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[Neuroleptic malignant syndrome--case report]. | 2001 |
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[Obsessive-compulsive disorders in adolescents with diagnosed schizophrenia]. | 2001 Jan-Feb |
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Effects of phenothiazine neuroleptics on the rate of caffeine demethylation and hydroxylation in the rat liver. | 2001 Nov-Dec |
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Prevalence of obesity in adolescent and young adult patients with and without schizophrenia and in relationship to antipsychotic medication. | 2001 Nov-Dec |
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Intracellular distribution of psychotropic drugs in the grey and white matter of the brain: the role of lysosomal trapping. | 2001 Oct |
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Effects of cytochrome P-450 inducers on the perazine metabolism in a primary culture of human hepatocytes. | 2003 Jul-Aug |
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Antipsychotic efficacy of the antidepressant trimipramine: a randomized, double-blind comparison with the phenothiazine perazine. | 2003 Mar-Apr |
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Acute psychosis with a mediastinal carcinoma metastasis. | 2005 Jan |
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Increased serum interleukin-1beta and interleukin-6 in elderly, chronic schizophrenic patients on stable antipsychotic medication. | 2005 Jun |
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Direct effects of neuroleptics on the activity of CYP2A in the liver of rats. | 2005 Nov-Dec |
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Characterization of human cytochrome p450 enzymes involved in the metabolism of the piperidine-type phenothiazine neuroleptic thioridazine. | 2006 Mar |
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Perazine and carbamazepine in comparison to olanzapine in schizophrenia. | 2007 |
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Simple and simultaneous determination for 12 phenothiazines in human serum by reversed-phase high-performance liquid chromatography. | 2007 Jul 1 |
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The activity of cytochrome P450 CYP2B in rat liver during neuroleptic treatment. | 2007 Sep-Oct |
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[Application of liquid chromatography coupled with mass spectrometry (LC/MS) to determine antidepressants in blood samples]. | 2008 Oct-Dec |
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Perazine at therapeutic drug concentrations inhibits human cytochrome P450 isoenzyme 1A2 (CYP1A2) and caffeine metabolism--an in vitro study. | 2009 Sep-Oct |
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[Perazine in the treatment of psychotic disorders--research review]. | 2010 May-Jun |
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Main contribution of the cytochrome P450 isoenzyme 1A2 (CYP1A2) to N-demethylation and 5-sulfoxidation of the phenothiazine neuroleptic chlorpromazine in human liver--A comparison with other phenothiazines. | 2010 Oct 15 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/11869638
Curator's Comment: In acutely ill and severely disturbed patients 50 mg perazine at time-intervals of 30 minutes can be administered intramuscularly
The customary dose range recommended for this antipsychotic under in-patient conditions is 75-600 mg/day (maximum 1000 mg/day).
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/19904008
About 80% of basal human CYP1A2 activity was reduced by the therapeutic concentrations of perazine (5-10 uM).
Substance Class |
Chemical
Created
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Record UNII |
8915147A2B
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Record Status |
Validated (UNII)
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Record Version |
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WHO-VATC |
QN05AB10
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WHO-ATC |
N05AB10
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NCI_THESAURUS |
C66883
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8042
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84-97-9
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Perazine
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C81093
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8915147A2B
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100000079987
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2100
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4744
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DTXSID6048628
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DB12710
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CHEMBL1697766
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D010464
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SUB14811MIG
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m8535
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201-578-9
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |